Tetrahydrofuran → tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-formylvalerate

HRID 1912104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912104
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:30](=[O:35])NCOC)[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(O)(=O)C>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([CH:30]=[O:35])[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 71114767tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-methoxymethylcarbamoylvalerate

Produkt 1

HCID 86675057tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-formylvalerateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-methoxymethylcarbamoylvalerate (4.61 g) and tetrahydrofuran (60 mL) were mixed. To the mixture was added dropwise diisobutylaluminum hydride (1.0 M in toluene) (13.1 mL) at −78° C. The mixture was stirred at −78° C. for 1.5 hr. To the mixture was added dropwise acetic acid (0.515 mL). After an addition of aqueous Rochelle salt at −20° C., the mixture was extracted with ethyl acetate. The organic layer washed with water, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/25) to give the title compound (2.60 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/25)

Quellen und Nachweise

ORD-Eintrag
ord-d4fcddd7217f4f609f18389659ed9d23
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604069B2

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